Acetonitrile → (4-bromophenyl)dimethylphosphine oxide

HRID 1845832Notes

Reaction equation

HRID 1845832 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][CH:3]=1.[CH3:9][PH:10](=[O:12])[CH3:11].CC#N>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([P:10](=[O:12])([CH3:11])[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 78041,4-DibromobenzeneHCID 178503022methylphosphonoylmethane

Product 1

HCID 59131561(4-bromophenyl)dimethylphosphine oxideYield 26%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

A solution of 1,4-dibromobenzene (2.35 g, 10 mmol), dimethylphosphine oxide (0.78 g, 10 mmol), and tetrakis(triphenylphosphine) palladium (0) (0.5 g) in nitrogen-purged CH3CN (20 mL) and triethylamine (5 mL) was heated at reflux for overnight. Then, the reaction mixture was concentrated and the residue was chromatographed on silica gel (0˜20 percent MeOH/DCM) to afford the product (600 mg, 26%) as a colorless solid; 1H NMR (CD3OD): δ 7.80-7.70 (m, 4H), 1.75 (d, 6H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for overnight
  3. concentrationThen, the reaction mixture was concentrated
  4. customthe residue was chromatographed on silica gel (0˜20 percent MeOH/DCM)

Sources & evidence

ORD record
ord-04979bb4bdc54a338839c0a48e22fbfc
Source dataset
uspto-grants-2015_02
Patent number
US08951993B2

Reaction notes

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